Priprava i identifikacija fenilferocenilmetilnih derivata

master's thesis

• Title (english): Synthesis and identification of phenylferrocenylmetyl derivatives
• Author: Katarina Škrlec
• Mentor: Sandra Jurić (mentor)
• Committee member: Sandra Jurić (predsjednik povjerenstva)
• Committee member: Mirela Matić (član povjerenstva)
• Committee member: Biljana Nigović (član povjerenstva)
• Granter: University of Zagreb; Faculty of Pharmacy and Biochemistry; (Department of organic chemistry); Zagreb
• Defense date and country: 2018-06-04, Croatia
• Scientific / art field, discipline and subdiscipline: BIOMEDICINE AND HEALTHCARE; Pharmacy; Medical Biochemistry

Abstract

Tema ovog diplomskog rada bila je organometalna kemija ferocena, konkretno sinteza izabranih monosupstituiranih ferocena. Sinteza se odvijala u tri koraka. U prvom stupnju, sintetizirani su fenilferocenilketoni reakcijom Friedel-Craftsova aciliranja. Nakon toga, u drugom koraku, ketoni su reducirani s LiAlH4 u odgovarajuće alkohole. Konačno, u zadnjem koraku pripravljen je ester reakcijom nukleofilne supstitucije između alkohola i acil-halogenida. Sintetizirane tvari analizirane su i identificirane metodom nuklearne magnetske rezonancije. Analizom NMR-spektara pripravljenih ferocenskih derivata utvrđeno je da različite vrste atoma daju različite kemijske pomake. Karakteristični kemijski pomaci aromatskih vodikovih atoma kreću se u rasponu od 4.00 ppm do 5.00 ppm za ferocen i od 7.00 ppm do 8.00 ppm za benzen, dok se kemijski pomak α-vodikovog atoma prelazeći iz fenilferocenilalkohola u ester mijenja od približno 5 ppm na 6.97 ppm zbog blizine karbonilnog kisikova atoma i većeg efekta odsjenjenja što uzrokuje i veći kemijski pomak. Kemijski pomaci aromatskih ugljikovih atoma kreću se unutar granica literaturnih podataka: ugljikovi atomi ferocena od 60 ppm do 80 ppm i ugljikovi atomi benzena od 90 ppm do 170 ppm. Kemijski pomaci karbonilnih ugljikovih atoma ketona (199 ppm) i estera (166 ppm) također su unutar granica literaturnih podataka.

Abstract (english)

The main subject of this diploma thesis was organometallic chemistry of ferrocene, particularly the synthesis of the chosen monosubstituted ferrocenes. The synthesis was performed in three steps. In the first step, phenylferrocenylketones were synthesized by the Friedel-Crafts acilation. After that, in the second step, the ketones were reduced with LiAlH4 into analogue alcohols. Finally, in the last step, an ester was prepared via nucleophilic substitution between alcohol and acyl-halide. Synthesized compounds were analyzed and identified by the method of nuclear magnetic resonance. Analysis of NMR-spectrums of the previously prepared ferrocene derivatives has shown that different atoms give different chemical shifts. The characteristic chemical shifts of the aromatic hydrogen atoms lay between 4.00 ppm and 5.00 ppm in case of ferrocene, and 7.00 pm and 8.00 ppm in case of benzene. The chemical shift of the α-hydrogen atom changes from approximately 5 ppm to 6.97 ppm because of the nearness of the carbonyl oxygen atom and the bigger effect of dishielding, which in the end leads to the larger chemical shift. The chemical shifts of the aromatic carbon atoms are in the intervals given in the literature: carbon atoms of the ferrocene are between 60 and 80 ppm, and the carbon atoms of the benzene are between 90 and 170 ppm. The chemical shifts of the carbonyl carbon atoms in the ketone (199 ppm) and ester (166 ppm) are also situated in the intervals given in the literature.

• Keywords: ferocen; nuklearna magnetska rezonancija; antitumorsko djelovanje
• Keywords (english): ferrocene; nuclear magnetic resonance; anticancer activity
• Language: croatian
• URN:NBN: urn:nbn:hr:163:716577
• Study programme: Title: Medical biochemistry; Study programme type: university; Study level: integrated undergraduate and graduate; Academic / professional title: magistar/magistra medicinske biokemije (magistar/magistra medicinske biokemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2018-11-28 16:21:13